HCID 59846150, compound → HCID 59846140, compound

HRID 605002Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=3)[C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:7][C:6]=2[C:5]1=[O:28]>C(Cl)(Cl)Cl.C(#N)C.[O-2].[O-2].[Mn+4]>[OH:1][CH2:2][CH2:3][N:4]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=3)[C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:7][C:6]=2[C:5]1=[O:28]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-(2-hydroxyethyl)-2-[4-(hydroxymethyl)phenyl]-3-phenyl-1,6-naphthyridin-5(6H)-one (35 mg, 0.094 mmol) in a mixture of chloroform (3 mL) and acetonitrile (3 mL) containing a suspension of activated manganese dioxide (230 mg, 2.6 mmol) was warmed at 70° C. for 1.5 hours. This suspension was filtered, rinsed with chloroform and the solvents evaporated. This residue was triturated with diethyl ether and some pure title compound was isolated by filtration. The mother liquors were subjected to column chromatography on silica gel and upon elution with 50-100% ethyl acetate/hexane and then 0.25-0.75% methanol/ethyl acetate additional product was obtained. 1H-NMR (500 MHz, CDCl3): δ 10.02 (1H, s), 8.74 (1H, s), 7.80 (2H, d, J=8 Hz), 7.62 (2H, d, J=8 Hz), 7.44 (1H, d, J=7.6 Hz), 7.27-7.31 (4H, m), 7.20-7.22 (2H, m), 6.89 (1H, d, J=7.5 Hz), 4.25 (2H, t, J=4.8 Hz), 4.04 (2H, br s), 2.56 (1H, br s).

Workup

additioncontaining
filtrationThis suspension was filtered
washrinsed with chloroform
customthe solvents evaporated
customThis residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-d1a63df71b68472b8d0eeeb59cf84a05
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910561B2

Reaction notes

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